Synthesis, complexation chemistry and a case of self-recognition of chiral phosphite ligands

Tetrahedron

Volumn 55, Issue 10, 1999, Pages 3071-3090

  Dros, Abert C ^a   Meetsma, Auke ^a   Kellogg, Richard M ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CATECHOL; LIGAND; PHOSPHITE; RESORCINOL;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033525451     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00067-8     Document Type: Article

References (33)

1. Gilheany, D.G. in The Chemistry of Organophosphorus Compounds, Vol. 1, Hartley, F.R., Ed.; Wiley, Chichester England, 1990; chapter 2 and references cited therein.
2. Levason, W. in The Chemistry of Organophosphorus Compounds, Vol. 1, Hartley, F.R., Ed., Wiley, Chichester England, 1992, p. 567.
3. Garrou, P.E. Chem. Rev. 1985, 85, 171.
4. Van Leeuwen, P.W.N.M.; Roobeek, C.F. J. Organomet. Chem. 1983, 258, 343.
5. Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
6. See Comprehensive Coordination Chemistry, Wilkinson, G.; Gillard, R.D.; McCleverty, J.A., Eds., Pergamon Press, Oxford, 1987.
7. Marynick, D.S. J. Am. Chem. Soc. 1984, 106, 4064.
8. Orpen, A.G.; Connelly, N.G. J. Chem. Soc., Chem. Commun. 1985, 1310.
9. McAuliffe, C.A.; Levason, W. Phosphine, Arsine and Stibine Complexes of the Transition Metals, Elsevier Scientific Publishing Company, Amsterdam, The Netherlands, 1979.
10. Tolman, C.A. Chem. Rev. 1977, 77, 313.
11. Kirtley, S.W. in Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F.G.A.; Abel, E.W., Eds., Pergamon Press, New York, 1982, Vol. 3, Chapter 26.1, p. 783.
12. Gray, G.M.; Fish, F.P.; Srivastava, D.K.; Varshney, A.; Van der Woerd, M.J.; Ealick, S.E. J. Organomet. Chem. 1990, 385, 49.
13. Gray, G.M.; Watt, W. J. Organomet. Chem. 1992, 434, 181.
14. (a) Bartish, C.M.; Kraihanzel, C.S. Inorg. Chem. 1973, 12, 391;
15. (b) Kraihanzel, C.S.; Bartish, C.M. Phosphorus 1974, 4, 271.
16. See Applied Homogeneous Catalysis with Organometallic Compounds, Cornils, B.; Herrmann, W.A., Eds., VCH Publishers, Weinheim, 1996.
17. (a) Ten Hoeve, W.; Wynberg, H. J. Org. Chem. 1985, 50, 4508;
18. (b) Hulst, R.; Zijlstra, R.W.J.; De Vries, N.K.; Feringa, B.L. Tetrahedron: Asymmetry 1994, 5, 1701.
19. Bailey, W.F.; Eliel, E.L. J. Am. Chem. Soc. 1974, 96, 1798.
20. Bentrude, W.G. in Phosphorus-31 NMR Spectral Properties in Compound Characterization and Structural Analysis, Quin, L.D.; Verkade, J.G., Eds., VCH Publishers, New York, 1994, p. 41.
21. Anteunis, M; Tavernier, D.; Borremans, F. Bull. Soc. Chim. Belges 1966, 75, 396.
22. Rodgers, J.; White, D.W.; Verkade, J.G. J. Chem. Soc. A 1971, 77.
23. Longeau, A.; Langer, F.; Knochel, P. Tetrahedron Lett. 1996, 37, 2209.
24. (a) Jugé, S.; Stephan, M.; Merdès, Genet, J.P.; Halut-Desportes, S. J. Chem. Soc., Chem. Commun. 1993, 531;
25. (b) Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.
26. Dros, A.C.; Zijlstra, R.W.J.; Van Duijnen, P.Th.; Spek, A.L.; Kooijman, H.; Kellogg, R.M. Tetrahedron 1998, 54, 7787.
27. Analogous to Munoz, A.; Hubert, C.; Luche, J.-L. J. Org. Chem. 1996, 61, 6015.
28. Braterman, P.S. Metal Carbonyl Complexes, Academic Press, London, 1975.
29. 2 see Wozniak, L.; Kowalski, W.; Chojnowski, J. Tetrahedron Lett. 1985, 26, 4965.
30. Babin, P.; Bennetau, B.; Dunoguès, J. Synth. Commun. 1992, 22, 2849.
31. Several methods for the determination of enantiomeric excesses rely upon (spectroscopic) measurement of the difference in properties between meso and racemic (or enantiomerically enriched) dimers formed by coupling to a bifunctional achiral derivatizing agent. These methods require for their success complete absence of chiral self-recognition. See, for example: (A) Feringa, B.L.; Smaardijk, A.; Wynberg, H. J. Am. Chem. Soc. 1985, 107, 4798;
32. (b) Vigneron, J.P.; Dhaenens, M.; Horeau, A. Tetrahedron 1973, 29, 1055.
33. 2 due to extensive fragmentation of the molecular ions under EI conditions.